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Preparation method of COMT inhibitor 5, 6, 7, 3', 4'-pentamethoxyl isoflavone

The technology of pentamethoxyisoflavone and inhibitor is applied in the field of chemical preparation, and achieves the effects of easy availability of raw materials, mild reaction conditions and simple operation.

Inactive Publication Date: 2010-02-10
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the chemical synthesis of 5,6,7,3',4'-pentamethoxyisoflavone (1) has not been reported so far

Method used

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  • Preparation method of COMT inhibitor 5, 6, 7, 3', 4'-pentamethoxyl isoflavone
  • Preparation method of COMT inhibitor 5, 6, 7, 3', 4'-pentamethoxyl isoflavone

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Embodiment 1

[0023] (1) Synthesis of 3,4-dimethoxyphenylacetyl chloride 2

[0024] Oxalyl chloride (5.8 mL, 11.6 mmol) was added dropwise to a solution of 3,4-dimethoxyphenylacetic acid (1.53 g, 7.8 mmol) in dichloromethane (2.0 mol / L, 10 mL) under the protection of argon, After the dropwise addition, heat the reaction mixture to reflux at 40-60° C. for 2 h, and cool to room temperature. The solvent and excess oxalyl chloride were removed under reduced pressure to obtain the product 3,4-dimethoxyphenylacetyl chloride 2, 1.67 g of a brown oil, with a yield of 100%. The product was directly used in the next reaction.

[0025] (2) Synthesis of 3,4-dimethoxyphenylacetic acid 3',4',5'-trimethoxyphenyl ester 3

[0026] Sodium hydride (dispersed in mineral oil, content 60%, 0.42g, 10.5mmol) was added to a solution of 3,4,5-trimethoxyphenol (1.20g, 6.5mmol) in tetrahydrofuran (10mL) under argon atmosphere The reaction mixture was stirred for 30 min under protection. Add compound 2 (1.67 g, 7.8...

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Abstract

The invention relates to a preparation method for COMT inhibitor 5, 6, 7, 3', 4'-pentamethoxyl isoflavone, comprising the following steps: mixing 3, 4-dimethoxyphenylacetic acid and oxalyl chloride indichloromethane solution to carry out reflux reaction for 2 to 3 h, and cooling to room temperature; adding 3, 4, 5-trimethoxy sodium phenolate to carry out esterification reaction to carry out Friesrearrangement reaction under the catalysis of Lewis acid boron trifluoride ether; and finally carrying out reaction with DMF with the existence of the Lewis acid boron trifluoride ether; and adding methane sulfonyl chloride to promote Vilsmeier-Haack formylation reaction and subsequent cyclization reaction to obtain light yellow crystals 5, 6, 7, 3', 4'-pentamethoxyl isoflavone. The preparation method has simple and easily available raw materials, simple operation, short reaction time, mild reaction condition, environment protection and high yield of 76 %, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of preparation of chemical drugs, in particular to a preparation method of COMT inhibitor 5,6,7,3',4'-pentamethoxyisoflavone. Background technique [0002] Dopamine (DA) is a recognized neurotransmitter in the brain, and its importance is reflected in the close relationship between the ascending neural pathway of DA and the regulation of body movement and mental activities of the human body. When these DA nervous systems malfunction, movement disorders will appear. Schizophrenia or depression in Kinson's disease and mental disorders. Catechol-O-methyltransferase (COMT) is an enzyme that exists widely in the human body. It degrades catecholamines by catalyzing the methylation of 3-hydroxyl groups. It is the main metabolizer of biologically active or toxic catecholamines. enzyme. It works with monoamine oxidase-B (MAO-B) to metabolize DA to homovanillic acid (HVA). [0003] In 1982, Gandhi Dasan et al. reported that ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61K31/352
Inventor 李洪启陈睿金叶李金星陈东玲
Owner DONGHUA UNIV
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